JPH0678246B2 - 診断用組成物 - Google Patents
診断用組成物Info
- Publication number
- JPH0678246B2 JPH0678246B2 JP60244240A JP24424085A JPH0678246B2 JP H0678246 B2 JPH0678246 B2 JP H0678246B2 JP 60244240 A JP60244240 A JP 60244240A JP 24424085 A JP24424085 A JP 24424085A JP H0678246 B2 JPH0678246 B2 JP H0678246B2
- Authority
- JP
- Japan
- Prior art keywords
- paramagnetic metal
- polymeric
- particles
- water
- composition according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims description 66
- 239000002245 particle Substances 0.000 claims description 135
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 90
- 229910052751 metal Inorganic materials 0.000 claims description 84
- 239000002184 metal Substances 0.000 claims description 84
- 230000005298 paramagnetic effect Effects 0.000 claims description 65
- 239000000126 substance Substances 0.000 claims description 61
- 239000000463 material Substances 0.000 claims description 41
- 229920000642 polymer Polymers 0.000 claims description 26
- 229920002472 Starch Polymers 0.000 claims description 25
- 239000008107 starch Substances 0.000 claims description 25
- 235000019698 starch Nutrition 0.000 claims description 24
- 150000001720 carbohydrates Chemical class 0.000 claims description 19
- 235000014633 carbohydrates Nutrition 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 230000002285 radioactive effect Effects 0.000 claims description 15
- 150000005846 sugar alcohols Chemical class 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 13
- 125000004429 atom Chemical group 0.000 claims description 13
- 150000004697 chelate complex Chemical class 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 150000004676 glycans Chemical class 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 229920001282 polysaccharide Polymers 0.000 claims description 11
- 239000005017 polysaccharide Substances 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 239000013522 chelant Substances 0.000 claims description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
- 239000012736 aqueous medium Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- 102000004139 alpha-Amylases Human genes 0.000 claims description 6
- 108090000637 alpha-Amylases Proteins 0.000 claims description 6
- 229940024171 alpha-amylase Drugs 0.000 claims description 6
- 239000007900 aqueous suspension Substances 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 5
- 239000002198 insoluble material Substances 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229920002307 Dextran Polymers 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- 229910052688 Gadolinium Inorganic materials 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000011651 chromium Substances 0.000 claims description 3
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 claims description 3
- 239000002195 soluble material Substances 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052692 Dysprosium Inorganic materials 0.000 claims description 2
- 229910052691 Erbium Inorganic materials 0.000 claims description 2
- 229910052693 Europium Inorganic materials 0.000 claims description 2
- 229910052689 Holmium Inorganic materials 0.000 claims description 2
- 102000004157 Hydrolases Human genes 0.000 claims description 2
- 108090000604 Hydrolases Proteins 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 claims description 2
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 claims description 2
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 claims description 2
- KJZYNXUDTRRSPN-UHFFFAOYSA-N holmium atom Chemical compound [Ho] KJZYNXUDTRRSPN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 239000002562 thickening agent Substances 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 230000003204 osmotic effect Effects 0.000 claims 1
- 239000000725 suspension Substances 0.000 description 77
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 66
- 239000012153 distilled water Substances 0.000 description 56
- 239000000243 solution Substances 0.000 description 39
- 239000006228 supernatant Substances 0.000 description 21
- 239000011324 bead Substances 0.000 description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 229960003330 pentetic acid Drugs 0.000 description 15
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- -1 dihydroxypropyl Chemical group 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 125000004430 oxygen atom Chemical group O* 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 8
- 238000004132 cross linking Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 6
- 210000001035 gastrointestinal tract Anatomy 0.000 description 6
- 239000002609 medium Substances 0.000 description 6
- 102000004169 proteins and genes Human genes 0.000 description 6
- 108090000623 proteins and genes Proteins 0.000 description 6
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 238000005119 centrifugation Methods 0.000 description 5
- 239000003431 cross linking reagent Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000007863 gel particle Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- RAEOEMDZDMCHJA-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-[2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]ethyl]amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CCN(CC(O)=O)CC(O)=O)CC(O)=O RAEOEMDZDMCHJA-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000003384 imaging method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- WDLRUFUQRNWCPK-UHFFFAOYSA-N Tetraxetan Chemical compound OC(=O)CN1CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC1 WDLRUFUQRNWCPK-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000012876 carrier material Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007822 coupling agent Substances 0.000 description 3
- 238000002405 diagnostic procedure Methods 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 125000000468 ketone group Chemical group 0.000 description 3
- 239000011572 manganese Substances 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 210000004291 uterus Anatomy 0.000 description 3
- NKIJBSVPDYIEAT-UHFFFAOYSA-N 1,4,7,10-tetrazacyclododec-10-ene Chemical compound C1CNCCN=CCNCCN1 NKIJBSVPDYIEAT-UHFFFAOYSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- URDCARMUOSMFFI-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-(2-hydroxyethyl)amino]acetic acid Chemical compound OCCN(CC(O)=O)CCN(CC(O)=O)CC(O)=O URDCARMUOSMFFI-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 2
- 229920000936 Agarose Polymers 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920001917 Ficoll Polymers 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 229930194542 Keto Natural products 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 125000002648 azanetriyl group Chemical group *N(*)* 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- RJOJUSXNYCILHH-UHFFFAOYSA-N gadolinium(3+) Chemical compound [Gd+3] RJOJUSXNYCILHH-UHFFFAOYSA-N 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 230000005291 magnetic effect Effects 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 210000000865 mononuclear phagocyte system Anatomy 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 229920001059 synthetic polymer Polymers 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- KBMBVTRWEAAZEY-UHFFFAOYSA-N trisulfane Chemical compound SSS KBMBVTRWEAAZEY-UHFFFAOYSA-N 0.000 description 2
- 238000002604 ultrasonography Methods 0.000 description 2
- 210000003932 urinary bladder Anatomy 0.000 description 2
- ZFTFOHBYVDOAMH-XNOIKFDKSA-N (2r,3s,4s,5r)-5-[[(2r,3s,4s,5r)-5-[[(2r,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-2-(hydroxymethyl)oxolan-2-yl]oxymethyl]-2-(hydroxymethyl)oxolane-2,3,4-triol Chemical class O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@@H]1[C@@H](O)[C@H](O)[C@](CO)(OC[C@@H]2[C@H]([C@H](O)[C@@](O)(CO)O2)O)O1 ZFTFOHBYVDOAMH-XNOIKFDKSA-N 0.000 description 1
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
- RAZLJUXJEOEYAM-UHFFFAOYSA-N 2-[bis[2-(2,6-dioxomorpholin-4-yl)ethyl]azaniumyl]acetate Chemical compound C1C(=O)OC(=O)CN1CCN(CC(=O)O)CCN1CC(=O)OC(=O)C1 RAZLJUXJEOEYAM-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- BDDLHHRCDSJVKV-UHFFFAOYSA-N 7028-40-2 Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O BDDLHHRCDSJVKV-UHFFFAOYSA-N 0.000 description 1
- 239000004382 Amylase Substances 0.000 description 1
- 102000013142 Amylases Human genes 0.000 description 1
- 108010065511 Amylases Proteins 0.000 description 1
- 229920000945 Amylopectin Polymers 0.000 description 1
- 229920000856 Amylose Polymers 0.000 description 1
- JXYACYYPACQCDM-UHFFFAOYSA-N Benzyl glycinate Chemical compound NCC(=O)OCC1=CC=CC=C1 JXYACYYPACQCDM-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 229920002670 Fructan Polymers 0.000 description 1
- 229920001503 Glucan Polymers 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 229920002527 Glycogen Polymers 0.000 description 1
- 101001132499 Homo sapiens RPA-related protein RADX Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229920001202 Inulin Polymers 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920001218 Pullulan Polymers 0.000 description 1
- 239000004373 Pullulan Substances 0.000 description 1
- 102100033967 RPA-related protein RADX Human genes 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019418 amylase Nutrition 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- WJKJXKRHMUXQSL-UHFFFAOYSA-N benzyl glycinate 4-methylbenzenesulfonate salt Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.NCC(=O)OCC1=CC=CC=C1 WJKJXKRHMUXQSL-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
- A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
- A61K49/10—Organic compounds
- A61K49/12—Macromolecular compounds
- A61K49/126—Linear polymers, e.g. dextran, inulin, PEG
- A61K49/128—Linear polymers, e.g. dextran, inulin, PEG comprising multiple complex or complex-forming groups, being either part of the linear polymeric backbone or being pending groups covalently linked to the linear polymeric backbone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
- A61K49/18—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes
- A61K49/1818—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles
- A61K49/1821—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles coated or functionalised microparticles or nanoparticles
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S436/00—Chemistry: analytical and immunological testing
- Y10S436/806—Electrical property or magnetic property
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/24—Nuclear magnetic resonance, electron spin resonance or other spin effects or mass spectrometry
Landscapes
- Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Radiology & Medical Imaging (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Nanotechnology (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8405501-1 | 1984-11-01 | ||
| SE8405500-3 | 1984-11-01 | ||
| SE8405501A SE465909B (sv) | 1984-11-01 | 1984-11-01 | Partikelformat diagnosticeringsmedel innehaallande en paramagnetisk metall |
| SE8405500A SE465908B (sv) | 1984-11-01 | 1984-11-01 | Diagnosticeringspartiklar innehaallande en paramagnetisk metall |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61155338A JPS61155338A (ja) | 1986-07-15 |
| JPH0678246B2 true JPH0678246B2 (ja) | 1994-10-05 |
Family
ID=26658808
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60244240A Expired - Lifetime JPH0678246B2 (ja) | 1984-11-01 | 1985-11-01 | 診断用組成物 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4985233A (da) |
| EP (1) | EP0184899B1 (da) |
| JP (1) | JPH0678246B2 (da) |
| DE (1) | DE3577185D1 (da) |
| DK (1) | DK164486C (da) |
| NO (1) | NO169525C (da) |
Families Citing this family (76)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0330801A1 (en) * | 1983-02-08 | 1989-09-06 | Schering Aktiengesellschaft | Ferromagnetic, diamagnetic or paramagnetic particles useful in the diagnosis and treatment of disease |
| US4735796A (en) * | 1983-12-08 | 1988-04-05 | Gordon Robert T | Ferromagnetic, diamagnetic or paramagnetic particles useful in the diagnosis and treatment of disease |
| US6203777B1 (en) * | 1983-12-21 | 2001-03-20 | Nycomed Imaging As | Method of contrast enhanced magnetic resonance imaging using carbohydrate particles |
| SE463651B (sv) * | 1983-12-21 | 1991-01-07 | Nycomed As | Diagnostikum och kontrastmedel |
| AU6621586A (en) * | 1985-11-18 | 1987-06-02 | University Of Texas System, The | Polychelating agents for image and spectral enhancement (and spectral shift) |
| US5336762A (en) * | 1985-11-18 | 1994-08-09 | Access Pharmaceuticals, Inc. | Polychelating agents for image and spectral enhancement (and spectral shift) |
| US5284646A (en) * | 1986-07-03 | 1994-02-08 | Advanced Magnetics Inc. | Hepatocyte specific receptor mediated endocytosis type magnetic resonance imaging contrast agents |
| US5352432A (en) * | 1986-07-03 | 1994-10-04 | Advanced Magnetics, Inc. | Hepatocyte specific composition and their use as diagnostic imaging agents |
| US5342607A (en) * | 1986-07-03 | 1994-08-30 | Advanced Magnetics, Inc. | Receptor mediated endocytosis type magnetic resonance imaging contrast agents |
| US4770183A (en) * | 1986-07-03 | 1988-09-13 | Advanced Magnetics Incorporated | Biologically degradable superparamagnetic particles for use as nuclear magnetic resonance imaging agents |
| US4951675A (en) * | 1986-07-03 | 1990-08-28 | Advanced Magnetics, Incorporated | Biodegradable superparamagnetic metal oxides as contrast agents for MR imaging |
| US5679323A (en) * | 1986-07-03 | 1997-10-21 | Advanced Magnetics, Inc. | Hepatocyte-specific receptor-mediated endocytosis-type compositions |
| US5219554A (en) | 1986-07-03 | 1993-06-15 | Advanced Magnetics, Inc. | Hydrated biodegradable superparamagnetic metal oxides |
| FR2612400A1 (fr) * | 1987-03-16 | 1988-09-23 | Centre Nat Rech Scient | Microcapsules contenant un marqueur radioactif et/ou paramagnetique sous forme de chelate, et leur utilisation dans le domaine de l'imagerie medicale |
| DE3709851A1 (de) * | 1987-03-24 | 1988-10-06 | Silica Gel Gmbh Adsorptions Te | Nmr-diagnostische fluessigkeitszusammensetzungen |
| DE3710730A1 (de) * | 1987-03-31 | 1988-10-20 | Schering Ag | Substituierte komplexbildner, komplexe und komplexsalze, verfahren zu deren herstellung und diese enthaltende pharmazeutische mittel |
| US5049667A (en) * | 1987-04-14 | 1991-09-17 | Guerbet S.A. | Nitrogen-containing cyclic ligands |
| US5154179A (en) * | 1987-07-02 | 1992-10-13 | Medical Magnetics, Inc. | Device construction and method facilitating magnetic resonance imaging of foreign objects in a body |
| DE3724188C2 (de) * | 1987-07-17 | 1995-05-18 | Heinz Dr Gries | Metallhaltige Oligosaccharid-Polysulfate, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Mittel |
| US6013531A (en) * | 1987-10-26 | 2000-01-11 | Dade International Inc. | Method to use fluorescent magnetic polymer particles as markers in an immunoassay |
| GB8801646D0 (en) * | 1988-01-26 | 1988-02-24 | Nycomed As | Chemical compounds |
| GB8813144D0 (en) * | 1988-06-03 | 1988-07-06 | Nycomed As | Compositions |
| JPH04501218A (ja) | 1988-08-04 | 1992-03-05 | アドヴァンスド マグネティックス インコーポレーティッド | 受容体媒介エンドサイト―シス型mri造影剤 |
| US5213788A (en) * | 1988-09-29 | 1993-05-25 | Ranney David F | Physically and chemically stabilized polyatomic clusters for magnetic resonance image and spectral enhancement |
| US5314681A (en) * | 1988-12-23 | 1994-05-24 | Nycomed Innovation Ab | Composition of positive and negative contrast agents for electron spin resonance enhanced magnetic resonance imaging |
| US5393525A (en) * | 1989-07-21 | 1995-02-28 | Nycomed Imaging As | Contrast medium comprising superparamagnetic or ferromagnetic particles capable of increasing viscosity after administration |
| GB8916782D0 (en) * | 1989-07-21 | 1989-09-06 | Nycomed As | Compositions |
| GB8916781D0 (en) * | 1989-07-21 | 1989-09-06 | Nycomed As | Compositions |
| GB8916780D0 (en) * | 1989-07-21 | 1989-09-06 | Nycomed As | Compositions |
| US5358702A (en) * | 1990-04-10 | 1994-10-25 | Unger Evan C | Methoxylated gel particle contrast media for improved diagnostic imaging |
| US5368840A (en) * | 1990-04-10 | 1994-11-29 | Imarx Pharmaceutical Corp. | Natural polymers as contrast media for magnetic resonance imaging |
| ATE153860T1 (de) * | 1990-04-10 | 1997-06-15 | Imarx Pharmaceutical Corp | Polymere und ihre verwendung als kontrastmittel bei der bilderzeugung mit magnetischer resonanz |
| US5215680A (en) * | 1990-07-10 | 1993-06-01 | Cavitation-Control Technology, Inc. | Method for the production of medical-grade lipid-coated microbubbles, paramagnetic labeling of such microbubbles and therapeutic uses of microbubbles |
| US5268165A (en) * | 1990-10-16 | 1993-12-07 | Biomedical Frontiers, Inc. | Polymer-deferoxamine-ferric iron adducts for use in magnetic resonance imaging |
| US5236693A (en) * | 1990-11-14 | 1993-08-17 | Brigham And Women's Hospital | Medical ultrasound contrast agent and method of using same |
| US5370901A (en) * | 1991-02-15 | 1994-12-06 | Bracco International B.V. | Compositions for increasing the image contrast in diagnostic investigations of the digestive tract of patients |
| GB9106686D0 (en) * | 1991-03-28 | 1991-05-15 | Hafslund Nycomed As | Improvements in or relating to contrast agents |
| US5310539A (en) * | 1991-04-15 | 1994-05-10 | Board Of Regents, The University Of Texas System | Melanin-based agents for image enhancement |
| DE4115789A1 (de) * | 1991-05-10 | 1992-11-12 | Schering Ag | Makrocyclische polymer-komplexbildner, deren komplexe, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel |
| WO1992021382A1 (en) * | 1991-06-03 | 1992-12-10 | Holmes, Michael, John | Improvements in or relating to contrast agents |
| JP2939336B2 (ja) * | 1991-06-11 | 1999-08-25 | 名糖産業株式会社 | 水溶性カルボキシ多糖−磁性酸化鉄酸化複合体 |
| DE69203080T2 (de) * | 1991-06-17 | 1996-02-01 | Dade International Inc., Deerfield, Ill. | Verfahren zur Herstellung magnetisch empfindlicherPolymerpartikel und ihre Anwendung. |
| US5250284A (en) * | 1991-10-15 | 1993-10-05 | Arnon Krongrad | Method for increasing nuclear magnetic resonance signals in living biological tissue using zinc |
| JPH07501331A (ja) * | 1991-11-19 | 1995-02-09 | イマアーレクス・フアーマシユーチカル・コーポレーシヨン | 改良された診断用の造影のためのゲル粒子造影剤 |
| GB9200388D0 (en) * | 1992-01-09 | 1992-02-26 | Nycomed As | Improvements in or relating to contrast agents |
| JP2911674B2 (ja) * | 1992-02-20 | 1999-06-23 | 明治乳業株式会社 | 消化管造影用組成物 |
| EP0565930A1 (en) * | 1992-03-27 | 1993-10-20 | Nihon Medi-Physics Co., Ltd. | Tetraazacyclododecane tetraacetic acid derivatives and the use thereof as diagnostic agents |
| DK0580878T3 (da) * | 1992-06-01 | 1996-02-12 | Basf Ag | Anvendelse af dispersioner af magneto-ioniske partikler som MRI-kontrastmedier |
| WO1994002068A1 (en) * | 1992-07-21 | 1994-02-03 | The General Hospital Corporation | System of drug delivery to the lymphatic tissues |
| WO1994009056A1 (en) * | 1992-10-14 | 1994-04-28 | Sterling Winthrop Inc. | Chelating polymers |
| US5817292A (en) * | 1992-10-14 | 1998-10-06 | Nycomed Imaging As | MR imaging compositions and methods |
| JPH08502300A (ja) * | 1992-10-14 | 1996-03-12 | スターリング ウィンスロップ アイエヌシー. | 治療および診断像形成組成物および方法 |
| US5401492A (en) * | 1992-12-17 | 1995-03-28 | Sterling Winthrop, Inc. | Water insoluble non-magnetic manganese particles as magnetic resonance contract enhancement agents |
| CA2154667A1 (en) * | 1993-02-02 | 1994-08-18 | Linda M. Gustavson | Directed biodistribution of small molecules |
| US5532006A (en) * | 1993-04-23 | 1996-07-02 | The Board Of Trustees Of The University Of Illinois | Magnetic gels which change volume in response to voltage changes for MRI |
| US6122540A (en) * | 1994-06-08 | 2000-09-19 | The Regents Of The University Of California | Noninvasive measurement of renal hemodynamic functions using magnetic resonance imaging |
| DE4428851C2 (de) * | 1994-08-04 | 2000-05-04 | Diagnostikforschung Inst | Eisen enthaltende Nanopartikel, ihre Herstellung und Anwendung in der Diagnostik und Therapie |
| ZA958789B (en) * | 1994-10-21 | 1996-05-29 | Nihon Mediphysics Co Ltd | Diagnostic imaging agent |
| DK81095A (da) * | 1995-07-11 | 1997-01-12 | Henrik S Thomsen | Peroralt MR-kontraststof til lever og øvre tarmkanal |
| FR2749082B1 (fr) * | 1996-05-24 | 1998-06-26 | Bio Merieux | Particules superparamagnetiques et monodispersees |
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| US2862920A (en) * | 1956-06-07 | 1958-12-02 | Ohio Commw Eng Co | Ferrous carboxymethyl dextran |
| GB1175834A (en) * | 1966-04-07 | 1969-12-23 | Atomic Energy Authority Uk | Improvements in or relating to the Chemical Production of Metal-Containing Materials as Particles and other Configurations |
| US3563978A (en) * | 1968-05-15 | 1971-02-16 | Irving L Ochs | Polyvalent metal complexes of natural polymers |
| US3928581A (en) * | 1972-09-13 | 1975-12-23 | Astra Laekemedel Ab | Certain polymer-iron complexes for treatment of iron deficiency |
| SE431214B (sv) * | 1977-06-02 | 1984-01-23 | Klaus H Mosbach | Sett att framstella magnetiska polymerpartiklar som berare av en foretredesvis biologiskt aktiv substans |
| SE409694B (sv) | 1978-01-02 | 1979-09-03 | Odlund Bjorn Alf Ingemar | Lastningsmaskin |
| US4370476A (en) * | 1979-07-17 | 1983-01-25 | Usher Thomas C | Dextran polycarboxylic acids, ferric hydroxide complexes |
| DE3129906C3 (de) * | 1981-07-24 | 1996-12-19 | Schering Ag | Paramagnetische Komplexsalze, deren Herstellung und Mittel zur Verwendung bei der NMR-Diagnostik |
| US4647447A (en) * | 1981-07-24 | 1987-03-03 | Schering Aktiengesellschaft | Diagnostic media |
| US4452773A (en) * | 1982-04-05 | 1984-06-05 | Canadian Patents And Development Limited | Magnetic iron-dextran microspheres |
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| US4675173A (en) * | 1985-05-08 | 1987-06-23 | Molecular Biosystems, Inc. | Method of magnetic resonance imaging of the liver and spleen |
| US4822594A (en) * | 1987-01-27 | 1989-04-18 | Gibby Wendell A | Contrast enhancing agents for magnetic resonance images |
-
1985
- 1985-10-25 DE DE8585307738T patent/DE3577185D1/de not_active Expired - Lifetime
- 1985-10-25 EP EP85307738A patent/EP0184899B1/en not_active Expired - Lifetime
- 1985-10-31 DK DK500085A patent/DK164486C/da active
- 1985-10-31 NO NO854349A patent/NO169525C/no unknown
- 1985-11-01 JP JP60244240A patent/JPH0678246B2/ja not_active Expired - Lifetime
- 1985-11-01 US US06/793,899 patent/US4985233A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| NO169525B (no) | 1992-03-30 |
| EP0184899B1 (en) | 1990-04-18 |
| DK164486C (da) | 1992-11-23 |
| NO169525C (no) | 1992-07-08 |
| EP0184899A1 (en) | 1986-06-18 |
| US4985233A (en) | 1991-01-15 |
| JPS61155338A (ja) | 1986-07-15 |
| DK500085D0 (da) | 1985-10-31 |
| DK164486B (da) | 1992-07-06 |
| DE3577185D1 (de) | 1990-05-23 |
| NO854349L (no) | 1986-05-02 |
| DK500085A (da) | 1986-05-02 |
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